Bennett, a train driver born in Shapwick, Dorset, was one of the top British middle-distance runners in his years, winning the AAA 4-mile (6.4 km) championship in 1897, and the cross country running title in 1899 and 1900. In the latter year, also the Olympic year, he won the British title in the mile, qualifying himself for the 1500 m in Paris. That distance had a rather weak field, and Bennett lead throughout the race, defeating local favourite Henri Deloge in 4:06.0. That time was an official world record, although many athletes had already run faster in competitions over the slightly longer mile.

Together with the combined British/Australian5000 metres team, Bennett won a second Olympic title. Bennett finished first in the race, with an unofficial world record 15:29.2, beating teammate John Rimmer. His third event was the 4000 m steeplechase, in which he just failed to catch up with the same Rimmer in the final part of the race, settling for second place.

His Olympic achievements were largely forgotten for more than 100 years until his grandson Chris Bennett found his abandoned and overgrown grave in the corner of St Andrew’s Churchyard in Kinson. In December 2011 Bennett was commemorated after Anthony Ives Memorials of Bournemouth donated a proper headstone to recognise his feat. The plinth, unveiled on the eve of the year of the London Olympics, reads: "In loving memory of Charles Bennett 1870-1948. First British track and field athlete to become Olympic Champion. Bennett, known as the Shapwick Express, won two gold medals and a silver at the Paris Games in 1900." The new headstone also remembers Bennett's wife Sarah Lena and reads: "Until the day break."